Ethyl chloroformate → HCID 14171567, compound

HRID 1639248Notes

Reaction equation

HRID 1639248 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[Cl:15].C(=O)(O)[O-].[Na+].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCl>[Cl:15][C:9]1[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=1[C:7]([C:3]1[N:2]([NH:1][C:23](=[O:24])[O:25][CH2:26][CH3:27])[CH:6]=[CH:5][CH:4]=1)=[O:16]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 14371423HCID 14371423, compound

Product 1

HCID 14171567HCID 14171567, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred slurry of 1-amino-2-(2,4-dichlorobenzoyl)pyrrole (377.6 g) and sodium bicarbonate (286.0 g) in 2.0 L of dichloromethane was added ethyl chloroformate (176.90 g) over 10 min. The reaction mixture was heated at reflux for 4 hrs and then quenched with H2O. The organic layer was washed with brine, dried (MgSO4), charcoaled, filtered and concentrated to a maroon oil. This oil was purified by flash chromatography (silica, dichloromethane) and concentrated to a green powder which was recrystallized from ether to give 171.8 g of white crystals, mp 114°-116°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hrs
  3. customquenched with H2O
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a maroon oil
  8. customThis oil was purified by flash chromatography (silica, dichloromethane)
  9. concentrationconcentrated to a green powder which
  10. customwas recrystallized from ether

Sources & evidence

ORD record
ord-60097de9b8344273874c0c25cd0ca484
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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